glove, n. — Green’s Dictionary of Slang

glove n.

1. some form of unspecified drinking-vessel [see cit. 1609, where the term is used in a list of similar containers].

1609

Dekker Gul’s Horne-booke Proem. 8: The Englishmans healthes, his hoopes, cans, half-cans, Gloues, Frolicks, and flap-dragons.

2. a condom [note Williams for 17C use of glove as metaphor for vagina].

c.1850		Peeping Tom (London) 15 60/3: You friend’s expedient cannot be relied upon. When the delirium of enjoyment becomes predominant his plan becomes impracticable [...] The only safe remedy is by the use of ‘gloves’.
1999		J. Ridley Love Is a Racket 385: You don’t cock me without a glove.
1999		G. Seal Lingo 126: In Lingo, condoms are [...] a glove.
2013		K. Koke ‘Fire in the Booth’ 🎵 She don't want my DNA so when we fuck I wear my gloves.

SE in slang uses

In phrases

go (in) for the gloves (v.)

1. to bet heavily, esp. beyond one’s means.

1865		Sporting Gaz. (London) 8 Apr. 4/3: To go for the gloves — To lay a large sum against a horse without the slightest intention of paying if he wins.
1867		S.A. Advertiser (Adelaide) 4 Apr. 3/7: And, finally, don’t patronise the glover— in other words, do not ‘go in for the gloves’.
1881		N.Z. Observer (Auckland) 8 Jan. 163/3: When a man plunges very heavily, knowing he can’t pay if he loses, it is called ‘going for the gloves’.
1889		H. Smart Long Odds I 113: ‘It’s neck or nothing this time, old man. I’ve got every acre of Temple Rising on it. I’m going for the gloves, and intend to be a man or a mouse over thi’".
1892		Queenscliff Sentinel (Vic.) 16 July 3/4: ‘I ask you to be guided by me once more, and lay all you can against Sunlight at the short price.’ ‘What! go for the gloves, you mean, on the principle that you may as well be hanged for a sheep as a lamb’.
1901		Queenslander (Brisbane) 20 Apr. 757: My dear Holmes, don’t get excited. I always have had a taste for long odds. So I’ll go for the gloves.
1913		Examiner (Launceston, Tas.) 24 Mar. 7/6: ‘I’m going for the gloves to-night - which means, I’m going to get back all my losses, or—’ he made an expressive gesture.
1921		Kalgoorlie Miner 1 Nov. 6/7: The old race of plungers has to all intents and purposes died right out. Men do not go for the gloves as once they were wont to do, and nowadays a comparatively small outlay will make a horse favourite.
1933		W. Argus Kalgoorlie, WA) 27 June 32/1: Usually fellow bookmakers are the sufferers when a bookmaker decides to go for the gloves.
1949		Queensland Times (Ipswich, Qld) 21 Oct. 5/3: Deep down in Andrew was some instinct which leapt to meet a sporting wager, and when he fully believed in a man as he believed in Vernis he was apt to throw caution to the four winds and go for the gloves.

2. in non-racing use, to commit onself unequivocally; in cites 1881, 1882 to propose marriage.

1881		Australian Town & Country Jrnl (Sydney) 11 June 31/1: From what I hear, however, you cannot be going for the gloves, as the fair lady in question has apparently made her choice.
1882		South Australian Weekly Chronicle (Adelaide) 23 Dec. 3S: He was devoted to Aline Atherstone, and manifestly intended to ‘go for the gloves’ there. In his own estimation of things he thought it would not be a bad match .
1900		Fitzroy City Press (Vic.) 31 Aug. 4/2: ‘I'm going for the gloves.’ [...] ‘What do you mean by you're going for the gloves?’ ‘I mean that probably by this time to-morrow I shall have either won you or lost you for ever’.
1931		Cairns Post (Qld) 25 June 12/4: the North Queensland League, in justice to the large numbers of players whose interests their constitution demands that they protect [...] should adopt more forceful methods and ‘Go for the gloves’.